JP2007523097A - Substituted azole compounds and their production and use - Google Patents
Substituted azole compounds and their production and use Download PDFInfo
- Publication number
- JP2007523097A JP2007523097A JP2006553419A JP2006553419A JP2007523097A JP 2007523097 A JP2007523097 A JP 2007523097A JP 2006553419 A JP2006553419 A JP 2006553419A JP 2006553419 A JP2006553419 A JP 2006553419A JP 2007523097 A JP2007523097 A JP 2007523097A
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- JP
- Japan
- Prior art keywords
- alkyl
- alkoxycarbonyl
- alkoxy
- haloalkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003851 azoles Chemical class 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 11
- 239000000417 fungicide Substances 0.000 claims abstract description 11
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229910004013 NO 2 Inorganic materials 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 241000238631 Hexapoda Species 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000002917 insecticide Substances 0.000 claims description 7
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004643 (C1-C12) haloalkoxy group Chemical group 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000005147 halomethylbenzenes Chemical class 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 44
- 201000010099 disease Diseases 0.000 abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 15
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- 240000008067 Cucumis sativus Species 0.000 abstract description 9
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 9
- 206010035148 Plague Diseases 0.000 abstract description 8
- 241000607479 Yersinia pestis Species 0.000 abstract description 8
- 241000221785 Erysiphales Species 0.000 abstract description 7
- 241000233679 Peronosporaceae Species 0.000 abstract description 6
- 235000007688 Lycopersicon esculentum Nutrition 0.000 abstract description 5
- 240000003768 Solanum lycopersicum Species 0.000 abstract description 5
- 235000009754 Vitis X bourquina Nutrition 0.000 abstract description 5
- 235000012333 Vitis X labruscana Nutrition 0.000 abstract description 5
- 240000006365 Vitis vinifera Species 0.000 abstract description 5
- 235000014787 Vitis vinifera Nutrition 0.000 abstract description 5
- 230000000749 insecticidal effect Effects 0.000 abstract description 5
- 240000007594 Oryza sativa Species 0.000 abstract description 4
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 4
- 230000000895 acaricidal effect Effects 0.000 abstract description 4
- 235000009566 rice Nutrition 0.000 abstract description 4
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- 235000005822 corn Nutrition 0.000 abstract description 3
- 240000004160 Capsicum annuum Species 0.000 abstract description 2
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 abstract description 2
- 235000007862 Capsicum baccatum Nutrition 0.000 abstract description 2
- 241000238371 Sepiidae Species 0.000 abstract description 2
- 239000001728 capsicum frutescens Substances 0.000 abstract description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 2
- 241000254173 Coleoptera Species 0.000 abstract 1
- 241001477931 Mythimna unipuncta Species 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 12
- 241000196324 Embryophyta Species 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 238000003359 percent control normalization Methods 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- SMQZZQFYHUDLSJ-UHFFFAOYSA-L disodium;1-dodecylnaphthalene;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.C1=CC=C2C(CCCCCCCCCCCC)=CC=CC2=C1 SMQZZQFYHUDLSJ-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- MGUDGDSNHPKOLL-DHZHZOJOSA-N methyl (e)-2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoate Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CBr MGUDGDSNHPKOLL-DHZHZOJOSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
- RPHPBUPJAHBWNY-UHFFFAOYSA-N 3-(4-nitrophenyl)-2h-1,2-oxazol-5-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC(=O)ON1 RPHPBUPJAHBWNY-UHFFFAOYSA-N 0.000 description 2
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 241000233654 Oomycetes Species 0.000 description 1
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- 241000500437 Plutella xylostella Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
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- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- PODVGHFHXJZNSG-UHFFFAOYSA-L calcium;dodecylbenzene;sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1 PODVGHFHXJZNSG-UHFFFAOYSA-L 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
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- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DGCZHKABHPDNCC-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)C=C1 DGCZHKABHPDNCC-UHFFFAOYSA-N 0.000 description 1
- NGRXSVFCLHVGKU-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C([N+]([O-])=O)C=C1 NGRXSVFCLHVGKU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
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- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- JUAHKSBERRLSHD-UHFFFAOYSA-N tetraphenyl-$l^{5}-phosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JUAHKSBERRLSHD-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/12—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本発明は、農業用殺虫剤および殺菌剤に関するものであり、置換アゾール化合物、その製造および適用を開示する。本発明の置換アゾール化合物は、式（Ｉ）として表される。本発明の化合物は、幅広い殺菌活性を有し、様々な作物の様々な疾患を防止かつ防除するのに用いることができる。たとえば、キュウリのべと病、キュウリの灰色カビ病、キュウリのうどん粉病、トマトの夏疫病、トマトの疫病、トウガラシの疫病、ブドウのべと病、ブドウの白腐れ病、リンゴの輪腐れ病、リンゴの斑点病、イネ紋枯れ病、イネのいもち病、コムギ赤錆病、コムギの葉枯れ病、コムギのうどん粉病、ナタネスクレロチニア病、トウモロコシのごま葉枯れ病等々のような疾患を防除するのに優れている。いくつかの化合物は、良好な殺虫活性および殺ダニ活性を有し、様々な作物の疫病およびコナダニを防除するのに用いることができる。たとえば、アワヨトウムシ、コナガ、アリマキおよびイエカを防除するのに用いられる。 The present invention relates to agricultural pesticides and fungicides and discloses substituted azole compounds, their manufacture and application. The substituted azole compounds of the present invention are represented as formula (I). The compounds of the present invention have a wide range of fungicidal activities and can be used to prevent and control various diseases of various crops. For example, cucumber downy mildew, cucumber gray mold, cucumber powdery mildew, tomato summer plague, tomato plague, red pepper plague, grape downy mildew, grape white rot, apple ring rot, Control diseases such as apple spot disease, rice blight, rice blast, wheat red rust, wheat leaf blight, wheat powdery mildew, rapeseed disease, corn sesame leaf blight, etc. It is excellent for. Some compounds have good insecticidal and acaricidal activity and can be used to control various crop plagues and acarids. For example, it is used to control armyworms, longhorn beetles, aphids and cuttlefish.
Description
本発明は、殺真菌剤または殺虫剤、特に置換アゾール化合物、およびその製法、ならびにその使用に関する。 The present invention relates to fungicides or insecticides, in particular substituted azole compounds, their preparation and their use.
ストロビルリン（ｓtrobilurin：メトキシアクリラート）化合物は、天然の産物であり、生物学的活性によって知られている。広いスペクトルを有する殺真菌剤のピラクロストロビン（pyraclostrobin）は、US5,869,517、US6,054,592、CN1,154,692AおよびCN1,308,065Aに開示された。ピラクロストロビンの構造は下記のとおりである： Strobilurin (methoxyacrylate) compounds are natural products and are known for their biological activity. The broad spectrum fungicide pyraclostrobin has been disclosed in US 5,869,517, US 6,054,592, CN 1,154,692A and CN 1,308,065A. The structure of pyraclostrobin is as follows:
殺真菌活性を有する下記の化合物も、DE19,548,786に開示された： The following compounds having fungicidal activity were also disclosed in DE 19,548,786:
殺真菌活性を有する下記の化合物は、特許のWO99/33812で公知である： The following compounds with fungicidal activity are known from patent WO99 / 33812:
上記化合物は、本発明に類似するが、いくつかの明らかな相違がある。 While the above compounds are similar to the present invention, there are some obvious differences.
発明の開示
本発明の目的は、非常に低い用量ですべての種類の植物疾患および昆虫に対する生物学的活性を有する置換アゾール化合物を提供することであり、化合物は、植物における疾患および昆虫を防除するために農業に適用することができる。
本発明の詳しい説明は、以下のとおりである：
DISCLOSURE OF THE INVENTION An object of the present invention is to provide substituted azole compounds having biological activity against all kinds of plant diseases and insects at very low doses, which compounds control diseases and insects in plants. Can be applied to agriculture.
A detailed description of the present invention is as follows:
本発明は、一般式（Ｉ）： The present invention is directed to general formula (I):
［式中、Ｘ1は、ＣＨまたはＮから選ばれ；Ｘ2は、Ｏ、ＳまたはＮＲ7から選ばれ；Ｘ3は、Ｏ、ＳまたはＮＲ8から選ばれ；
Ａ1は、ＮまたはＣＲ9から選ばれ；Ａ2は、ＮまたはＣＲ10から選ばれ；Ａ3は、ＮまたはＣＲ11から選ばれ；Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれる。
Ｒ1、Ｒ2は、同じであっても、異なってもよくて、Ｈ、Ｃ1〜Ｃ12アルキルまたはＣ1〜Ｃ12ハロアルキルから選ばれ；
Ｒ3は、Ｈ、ハロ、Ｃ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルキルまたはＣ1〜Ｃ12アルコキシから選ばれ；
Ｒ7は、ＨまたはＣ1〜Ｃ12アルキルから選ばれ；
Ｒ8は、Ｈ、Ｃ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルキル、Ｃ1〜Ｃ12アルコキシカルボニルまたはＣ1〜Ｃ12アルコキシカルボニルＣ1〜Ｃ12アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11は、同じであっても、異なってもよくて、Ｈ、ハロ、ＮＯ2、ＣＮ、ＣＯＮＨ2、ＣＨ2ＣＯＮＨ2、ＣＨ2ＣＮ、Ｃ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルキル、Ｃ1〜Ｃ12アルコキシ、Ｃ1〜Ｃ12ハロアルコキシ、Ｃ1〜Ｃ12アルキルチオ、Ｃ1〜Ｃ12アルキルスルホニル、Ｃ1〜Ｃ12アルキルカルボニル、Ｃ1〜Ｃ12アルコキシＣ1〜Ｃ12アルキル、Ｃ1〜Ｃ12アルコキシカルボニル、Ｃ1〜Ｃ12アルコキシカルボニルＣ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルコキシＣ1〜Ｃ12アルキルから選ばれるか、または基は、任意の他の基：アミノＣ1〜Ｃ12アルキル、アリール、ヘテロアリールで置換されていてもよく；アロキシル、アリールＣ1〜Ｃ12アルキル、アリールＣ1〜Ｃ12アルコキシ、ヘテロアリールＣ1〜Ｃ12アルキルもしくはヘテロアリールＣ1〜Ｃ12アルコキシから選ばれる］
で示される置換アゾール化合物および立体異性体を提供する。
[Wherein X 1 is selected from CH or N; X 2 is selected from O, S or NR 7 ; X 3 is selected from O, S or NR 8 ;
A 1 is selected from N or CR 9 ; A 2 is selected from N or CR 10 ; A 3 is selected from N or CR 11 ; if N is selected, then A 1 , A 2 or A Only one of 3 is selected from N.
R 1 and R 2 may be the same or different and are selected from H, C 1 -C 12 alkyl or C 1 -C 12 haloalkyl;
R 3 is selected from H, halo, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl or C 1 -C 12 alkoxy;
R 7 is selected from H or C 1 -C 12 alkyl;
R 8 is selected from H, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxycarbonyl or C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and H, halo, NO 2 , CN, CONH 2 , CH 2 CONH 2 , CH 2 CN, C 1 ~C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 haloalkoxy C 1 -C Selected from 12 alkyl or the group may be substituted with any other group: amino C 1 -C 12 alkyl, aryl, heteroaryl; aroxyl, aryl C 1 -C 12 alkyl, aryl C 1 ~C 12 alkoxy Selected from heteroaryl C 1 -C 12 alkyl or heteroaryl C 1 -C 12 alkoxy]
The substituted azole compound and stereoisomer shown by these are provided.
本発明の一般式（Ｉ）の好適化合物では、
Ｘ1は、ＣＨまたはＮから選ばれ；Ｘ2は、Ｏ、ＳまたはＮＲ7から選ばれ；Ｘ3は、Ｏ、ＳまたはＮＲ8から選ばれ；
Ａ1は、ＮまたはＣＲ9から選ばれ、Ａ2は、ＮまたはＣＲ10から選ばれ、Ａ3は、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2は、同じであっても、異なってもよくて、Ｈ、Ｃ1〜Ｃ6アルキルまたはＣ1〜Ｃ6ハロアルキルから選ばれ；
Ｒ3は、Ｈ、ハロ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキルまたはＣ1〜Ｃ6アルコキシから選ばれ；
Ｒ7は、ＨまたはＣ1〜Ｃ6アルキルから選ばれ；
Ｒ8は、Ｈ、Ｃ1〜Ｃ6アルキル；Ｃ1〜Ｃ6ハロアルキル；Ｃ1〜Ｃ6アルコキシカルボニルまたはＣ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11は、同じであっても、異なってもよくて、Ｈ、ハロ、ＮＯ2、ＣＮ、ＣＯＮＨ2、ＣＨ2ＣＯＮＨ2、ＣＨ2ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルコキシＣ1〜Ｃ6アルキルから選ばれるか、または基は、任意の他の基：アミノＣ1〜Ｃ6アルキル、アリール、ヘテロアリール、アロキシル、アリールＣ1〜Ｃ6アルキル、アリールＣ1〜Ｃ6アルコキシ、ヘテロアリールＣ1〜Ｃ6アルキルもしくはヘテロアリールＣ1〜Ｃ6アルコキシで置換されていてもよい。
In preferred compounds of general formula (I) according to the invention,
X 1 is selected from CH or N; X 2 is selected from O, S or NR 7 ; X 3 is selected from O, S or NR 8 ;
A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 , A 3 is selected from N or CR 11, and if selected from N, A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 may be the same or different and are selected from H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R 3 is selected from H, halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy;
R 7 is selected from H or C 1 -C 6 alkyl;
R 8 is selected from H, C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxycarbonyl or C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and may be H, halo, NO 2 , CN, CONH 2 , CH 2 CONH 2 , CH 2. CN, C 1 ~C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy C 1 -C or selected from alkyl, or a group may be any other group: amino C 1 -C 6 alkyl, aryl, heteroaryl, Arokishiru, aryl C 1 -C 6 alkyl, aryl C 1 -C 6 alkoxy, heteroaryl C 1 ~C 6 alkyl Properly it may be substituted with a heteroaryl C 1 -C 6 alkoxy.
更に、本発明の一般式（Ｉ）の好適化合物では、
Ｘ1は、ＣＨまたはＮから選ばれ；Ｘ2は、ＯまたはＮＨから選ばれ；Ｘ3は、Ｏ、ＳまたはＮＲ8から選ばれ；
Ａ1は、ＮまたはＣＲ9から選ばれ、Ａ2は、ＮまたはＣＲ10から選ばれ、Ａ3は、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2は、ＣＨ3であり；
Ｒ3は、ＨまたはＣＨ3から選ばれ；
Ｒ8は、Ｈ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ3アルコキシカルボニルまたはＣ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ3アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11は、同じであっても、異なってもよくて、Ｈ、ハロ、ＮＯ2、ＣＮ、ＣＯＮＨ2、ＣＨ2ＣＯＮＨ2、ＣＨ2ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルコキシＣ1〜Ｃ6アルキルから選ばれるか、または基は、任意の他の基：アミノＣ1〜Ｃ3アルキル、フェニル、フェノキシ、ベンジルもしくはベンジルオキシで置換されていてもよい。
Furthermore, in the preferred compounds of general formula (I) of the present invention,
X 1 is selected from CH or N; X 2 is selected from O or NH; X 3 is selected from O, S or NR 8 ;
A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 , A 3 is selected from N or CR 11, and if selected from N, A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 are CH 3 ;
R 3 is selected from H or CH 3 ;
R 8 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 3 alkoxycarbonyl or C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and may be H, halo, NO 2 , CN, CONH 2 , CH 2 CONH 2 , CH 2. CN, C 1 ~C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy C 1 -C Selected from 6 alkyl or the group may be substituted with any other group: amino C 1 -C 3 alkyl, phenyl, phenoxy, benzyl or benzyloxy.
本発明の式（Ｉ）のなお一層好適な化合物では、
Ｘ1は、ＣＨまたはＮから選ばれ；Ｘ2は、ＯまたはＮＨから選ばれ；Ｘ3は、ＯまたはＮＲ8から選ばれ；
Ａ1は、ＮまたはＣＲ9から選ばれ、Ａ2は、ＮまたはＣＲ10から選ばれ、Ａ3は、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2は、ＣＨ3であり；
Ｒ3は、Ｈであり；
Ｒ8は、Ｈ、Ｃ1〜Ｃ3アルキル；Ｃ1〜Ｃ3ハロアルキル；Ｃ1〜Ｃ3アルコキシカルボニルまたはＣ1〜Ｃ3アルコキシカルボニルＣ1〜Ｃ3アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11は、同じであっても、異なってもよくて、Ｈ、Ｃｌ、Ｂｒ、Ｆ、ＮＯ2、ＣＮ、ＣＨ2ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ3アルキル、Ｃ1〜Ｃ3ハロアルコキシＣ1〜Ｃ3アルキル、置換アミノＣ1〜Ｃ3アルキル、フェニルもしくは置換フェニル、フェノキシもしくは置換フェノキシから選ばれる。
In still more preferred compounds of formula (I) of the present invention,
X 1 is selected from CH or N; X 2 is selected from O or NH; X 3 is selected from O or NR 8 ;
A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 , A 3 is selected from N or CR 11, and if selected from N, A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 are CH 3 ;
R 3 is H;
R 8 is selected from H, C 1 -C 3 alkyl; C 1 -C 3 haloalkyl; C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxycarbonyl C 1 -C 3 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and H, Cl, Br, F, NO 2 , CN, CH 2 CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 3 alkyl, C 1 -C 3 haloalkoxy C 1 -C 3 alkyl, substituted Selected from amino C 1 -C 3 alkyl, phenyl or substituted phenyl, phenoxy or substituted phenoxy.
本発明の式（Ｉ）の最も好適な化合物では、
Ｘ1は、ＣＨまたはＮから選ばれ；Ｘ2は、ＯまたはＮＨから選ばれ；Ｘ3は、ＯまたはＮＲ8から選ばれ；
Ａ1は、ＮまたはＣＲ9から選ばれ、Ａ2は、ＮまたはＣＲ10から選ばれ、Ａ3は、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2は、ＣＨ3であり；
Ｒ3は、Ｈであり；
Ｒ8は、Ｈ、Ｃ1〜Ｃ3アルキル；Ｃ1〜Ｃ3ハロアルキル；Ｃ1〜Ｃ3アルコキシカルボニルまたはＣ1〜Ｃ3アルコキシカルボニルＣ1〜Ｃ3アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11は、同じであっても、異なってもよくて、Ｈ、Ｃｌ、Ｂｒ、Ｆ、ＮＯ2、ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ3ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ3アルキル、フェニルもしくはハロフェニル、フェノキシもしくはハロフェノキシから選ばれる。
In the most preferred compounds of formula (I) of the present invention,
X 1 is selected from CH or N; X 2 is selected from O or NH; X 3 is selected from O or NR 8 ;
A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 , A 3 is selected from N or CR 11, and if selected from N, A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 are CH 3 ;
R 3 is H;
R 8 is selected from H, C 1 -C 3 alkyl; C 1 -C 3 haloalkyl; C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxycarbonyl C 1 -C 3 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different and may be H, Cl, Br, F, NO 2 , CN, C 1 -C 6 alkyl. , C 1 -C 3 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 3 alkyl, phenyl or halophenyl, selected from phenoxy or halophenoxy.
以下は、一般式（Ｉ）における用語の意味である：
フェノキシ、ベンジルオキシ、フェニル、ベンジルは、任意の位置において、Ｈ、アルキル、アルコキシ、ハロアルキル、ハロアルコキシ、ハロ、ＮＯ2またはＣＮ等々から選ばれる０〜５個の基で置換されていてもよい。
The following are the meanings of the terms in general formula (I):
Phenoxy, benzyloxy, phenyl, benzyl may be substituted at any position with 0-5 groups selected from H, alkyl, alkoxy, haloalkyl, haloalkoxy, halo, NO 2, CN, and the like.
ハロゲンまたはハロは、フルオロ、クロロ、ブロモおよびヨードを包含することを意味する。 Halogen or halo is meant to include fluoro, chloro, bromo and iodo.
アルキルは、メチル、エチル、プロピル、イソプロピルおよびtert−ブチルのような、直鎖状もしくは分枝鎖状のいずれかのアルキルを包含する。 Alkyl includes either straight or branched alkyl, such as methyl, ethyl, propyl, isopropyl and tert-butyl.
ハロアルキルは、水素原子がすべてか、または部分的にハロゲンで置換されていてもよい、直鎖もしくは分枝鎖アルキル、たとえばクロロメチル、ジクロロメチル、トリクロロメチル、フルオロメチル、ジフルオロメチル、トリフルオロメチルを言う。 Haloalkyl is a straight or branched alkyl, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, which may be all or partially substituted with halogen atoms. To tell.
アルコキシは、酸素原子によって構造に結合されている、直鎖または分枝鎖アルキルを言う。 Alkoxy refers to a straight or branched alkyl bonded to the structure by an oxygen atom.
ハロアルコキシは、水素原子がすべてか、または部分的にハロゲンで置換されていてもよい、直鎖もしくは分枝鎖アルコキシ、たとえばクロロメトキシ、ジクロロメトキシ、トリクロロメトキシ、フルオロメトキシ、ジフルオロメトキシ、トリフルオロメトキシ、クロロフルオロメトキシまたはトリフルオロエトキシを言う。 Haloalkoxy is a straight or branched alkoxy which may be all or partially substituted with halogens, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy Chlorofluoromethoxy or trifluoroethoxy.
アルケニルは、任意の位置で二重結合を有する、ビニルまたはアリルのような直鎖もしくは分枝鎖のものを意味する。置換アルケニルは、任意の位置において任意の基で置換された、アリールビニルを包含する。 Alkenyl means linear or branched, such as vinyl or allyl, having a double bond at any position. Substituted alkenyl includes arylvinyl substituted with any group at any position.
アルキニルは、任意の位置で三重結合を有する、直鎖または分枝鎖のもの、たとえばエチニル、プロピニルを言う。置換アルキニルは、任意の位置において任意の基で置換された、アリールエチニルを包含する。 Alkynyl refers to straight or branched chain, eg ethynyl, propynyl, having a triple bond at any position. Substituted alkynyl includes arylethynyl substituted with any group at any position.
アリール、およびアリールアルキル、アリールアルケニル、アリールアルキニル、アリールオキシ、アリールオキシアルキルにおけるアリールは、フェニルおよびナフチルを包含する。 Aryl and aryl in arylalkyl, arylalkenyl, arylalkynyl, aryloxy, aryloxyalkyl include phenyl and naphthyl.
本発明におけるヘテロアリールは、１個以上のＮ、Ｏ、Ｓなるヘテロ原子を含む五員環もしくは六員環、たとえばピリジン、フラン、ピリミジン、ピラジン、ピリダジン、トリアジン、キノリンまたはベンゾフランを言う。 Heteroaryl in the present invention refers to a five-membered or six-membered ring containing one or more heteroatoms of N, O, S, such as pyridine, furan, pyrimidine, pyrazine, pyridazine, triazine, quinoline or benzofuran.
異なる置換基へのＣ＝ＣまたはＣ＝Ｎ結合のために、本発明の化合物は、幾何異性体を形成し得る（異なる異性体は、それぞれ、ＺおよびＥで表される）。Ｚ異性体およびＥ異性体、ならびに任意の割合でのそれらの混合物は、本発明に包含される。 Due to C═C or C═N bonds to different substituents, the compounds of the invention may form geometric isomers (different isomers are represented by Z and E, respectively). The Z and E isomers, and mixtures thereof in any proportion are encompassed by the present invention.
本発明は、表１〜３中の下記の化合物によって説明されるが、それによって制約されるものではない。 The present invention is illustrated by the following compounds in Tables 1-3, but is not limited thereby.
本発明のいくつかの化合物の物理的および化学的特性、ならびに1Ｈ−ＮＭＲスペクトル（1Ｈ−ＮＭＲ、３００Hz、内部標準：ＴＭＳ、ＣＤＣｌ3）は、下記のとおりである： The physical and chemical properties and 1 H-NMR spectra ( 1 H-NMR, 300 Hz, internal standard: TMS, CDCl 3 ) of some compounds of the invention are as follows:
本発明のいくつかの化合物の物理的および化学的特性、ならびに1Ｈ−ＮＭＲスペクトル（1Ｈ−ＮＭＲ、３００Hz、内部標準：ＴＭＳ、ＣＤＣｌ3）は、下記のとおりである： The physical and chemical properties and 1 H-NMR spectra ( 1 H-NMR, 300 Hz, internal standard: TMS, CDCl 3 ) of some compounds of the invention are as follows:
本発明のいくつかの化合物の物理的および化学的特性、ならびに1Ｈ−ＮＭＲスペクトル（1Ｈ−ＮＭＲ、３００Hz、内部標準：ＴＭＳ、ＣＤＣｌ3）は、下記のとおりである： The physical and chemical properties and 1 H-NMR spectra ( 1 H-NMR, 300 Hz, internal standard: TMS, CDCl 3 ) of some compounds of the invention are as follows:
本発明は、式（Ｉ）を有する置換アゾール化合物の製法も包含する。 The present invention also includes a process for preparing a substituted azole compound having the formula (I).
それは、一般式（III）で示される、ヒドロキシル基を有するアゾール化合物と一般式（IV）で示されるハロメチルベンゼンとの、塩基の存在下での反応： It is a reaction of an azole compound having a hydroxyl group represented by the general formula (III) and a halomethylbenzene represented by the general formula (IV) in the presence of a base:
［式中、Ｒは、離脱基、たとえばＣｌまたはＢｒである］
によって製造することができる。その他の基は、上に定義されたとおりである。
[Wherein R is a leaving group such as Cl or Br]
Can be manufactured by. The other groups are as defined above.
挙げる適正な溶媒は、テトラヒドロフラン、アセトニトリル、トルエン、キシレン、ベンゼン、ＤＭＦ、ＤＭＳＯ、アセトンまたはブタノン等々から選ばれ得る。 Suitable solvents to mention may be selected from tetrahydrofuran, acetonitrile, toluene, xylene, benzene, DMF, DMSO, acetone or butanone and the like.
挙げる適正な塩基は、水酸化カリウム、水酸化ナトリウム、炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウム、トリエチルアミン、ピリジン、ナトリウムメトキシド、ナトリウムエトキシド、水素化ナトリウム、カリウムもしくはナトリウムtert−ブトキシド等々から選ばれ得る。 Suitable bases to be listed are selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium or sodium tert-butoxide and the like. obtain.
挙げる適正な温度は、室温ないし溶媒の沸点である。通常の温度は、２０〜１００℃である。 Appropriate temperatures listed are from room temperature to the boiling point of the solvent. Normal temperature is 20-100 degreeC.
反応は、３０分〜２０時間後、一般的には１〜１０時間後に終了し得る。 The reaction can be completed after 30 minutes to 20 hours, generally after 1 to 10 hours.
Ｘ1＝Ｎ、Ｘ2＝ＮＨである一般式（Ｉ）の化合物は、Ｘ1＝Ｎ、Ｘ2＝Ｏである一般式（Ｉ）の化合物とメチルアミンとの反応によって、容易に製造することができる。 A compound of the general formula (I) in which X 1 = N and X 2 = NH is easily prepared by reacting a compound of the general formula (I) in which X 1 = N and X 2 ═O with methylamine. be able to.
一般式（III）の中間体は、一般式（II）の中間体と（置換）ヒドラジンまたはヒドロキシアミンとの公知の方法による反応によって製造することができる。一般式（II）の中間体は、購入するか、または公知の方法に従って製造することができる（米国特許第3,781,438号、CN1,257,490A、WO96/15115等々を参照されたい）。 The intermediate of the general formula (III) can be produced by a reaction by a known method of the intermediate of the general formula (II) and (substituted) hydrazine or hydroxyamine. Intermediates of general formula (II) can be purchased or prepared according to known methods (see US Pat. No. 3,781,438, CN1,257,490A, WO96 / 15115, etc.).
一般式（III）で示される中間体のいくつかを表４に示す。一般式（IV）で示される中間体は、公知の方法に従って製造することができる（米国特許第4,723,034号および第5,545,578号を参照されたい）。 Table 4 shows some of the intermediates represented by the general formula (III). Intermediates of general formula (IV) can be prepared according to known methods (see US Pat. Nos. 4,723,034 and 5,545,578).
本発明のいくつかの中間体の物理的および化学的特性、ならびに1Ｈ−ＮＭＲスペクトル（1Ｈ−ＮＭＲ、３００Hz、内部標準：ＴＭＳ、ＣＤＣｌ3）は、下記のとおりである： The physical and chemical properties and 1 H-NMR spectra ( 1 H-NMR, 300 Hz, internal standard: TMS, CDCl 3 ) of some intermediates of the invention are as follows:
本発明は、殺虫剤および殺真菌剤の組成物も提供し、該組成物の有効成分は、一般式（Ｉ）で示される化合物であって、該有効成分は、０．１〜９９重量％の総量で存在する。 The present invention also provides a composition of an insecticide and a fungicide, wherein the active ingredient of the composition is a compound represented by the general formula (I), and the active ingredient is 0.1 to 99% by weight. Present in total amount.
本発明は、更には、該組成物をその上に製造する方法も提供する。一般式（Ｉ）の化合物、およびそれらの担体は、混合される。該組成物は、一成分化合物であっても、いくつかの成分との化合物の混合物であってもよい。 The present invention further provides a method for producing the composition thereon. The compounds of general formula (I) and their carriers are mixed. The composition may be a one-component compound or a mixture of compounds with several components.
本発明における担体は、必要条件に合致する：有効成分を用いて調製した後に、担体について処理しようとする部位に適用するのが容易である。たとえば、部位は、貯蔵、輸送または操作に簡便な植物、種子もしくは土壌であることができよう。担体は、固体、または通常は加圧下で気体状態から転換する液体を含む、液体であることができよう。そして、殺虫・殺菌組成物を調製するのに用いられる担体が適用される。 The carrier according to the invention meets the requirements: it is easy to apply to the site to be treated for the carrier after it has been prepared with the active ingredient. For example, the site could be a plant, seed or soil that is easy to store, transport or manipulate. The carrier could be a solid, or a liquid, including a liquid that normally converts from a gaseous state under pressure. And the carrier used for preparing an insecticidal / bactericidal composition is applied.
適切な固体担体は、天然および合成粘土ならびにケイ酸塩、たとえばケイ藻土、タルク、ケイ酸アルミニウムマグネシウム、ケイ酸アルミニウム（陶土）、モンモリロナイトおよび雲母；炭酸カルシウム；硫酸カルシウム；硫酸アンモニウム；合成酸化ケイ素および合成ケイ酸カルシウムまたはケイ酸アルミニウム；元素、たとえば炭素および硫黄；天然および合成樹脂、たとえばクマロン樹脂、ポリ塩化ビニル、ならびにスチレン重合体および共重合体；固体のポリクロロフェノール；瀝青；蝋、たとえば蜜蝋またはパラフィン蝋を包含する。 Suitable solid carriers include natural and synthetic clays and silicates such as diatomaceous earth, talc, magnesium aluminum silicate, aluminum silicate (porcelain), montmorillonite and mica; calcium carbonate; calcium sulfate; ammonium sulfate; synthetic silicon oxide and Synthetic calcium silicate or aluminum silicate; elements such as carbon and sulfur; natural and synthetic resins such as coumarone resin, polyvinyl chloride, and styrene polymers and copolymers; solid polychlorophenols; bitumen; waxes such as beeswax Or paraffin wax.
適切な液体担体は、水、イソプロパノールまたはアルコールのようなアルコール；アセトン、メチルエチルケトン、メチルイソプロピルケトンまたはシクロヘキサノンのようなケトン；エーテル；ベンゼン、キシレン、トルエンのような芳香族；灯油または鉱油のような石油留分、四塩化炭素、四塩化エチレンおよび／または三塩化エチレンのような塩素化脂肪族炭化水素を包含する。これらの異なる液体の混合物は、一般的に、適切であることがしばしばである。 Suitable liquid carriers are alcohols such as water, isopropanol or alcohol; ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone or cyclohexanone; ethers; aromatics such as benzene, xylene, toluene; petroleum such as kerosene or mineral oil Includes fractions, chlorinated aliphatic hydrocarbons such as carbon tetrachloride, ethylene tetrachloride and / or ethylene trichloride. Mixtures of these different liquids are often often appropriate.
殺虫剤および殺真菌剤の組成物は、しばしば、濃縮形態で配合されかつ輸送されて、次いで、使用者によって希釈された後に適用される。少量の界面活性剤の存在は、この希釈工程を促進する。したがって、好ましくは、本発明による組成物中の少なくとも一種の担体は、界面活性剤である。たとえば、該組成物は、少なくとも二種の担体を含有して、うち少なくとも一種は界面活性剤であってもよい。 Insecticide and fungicide compositions are often formulated and transported in concentrated form and then applied after dilution by the user. The presence of a small amount of surfactant facilitates this dilution process. Preferably, therefore, at least one carrier in the composition according to the invention is a surfactant. For example, the composition may contain at least two carriers, at least one of which may be a surfactant.
界面活性剤は、乳化剤、分散剤または湿潤剤であってもよく；非イオン性でもイオン性でもよい。適切な界面活性剤の例は、ポリアクリル酸およびリグニンスルホン酸のナトリウムまたはカルシウム塩；分子中に少なくとも１２個の炭素原子を有する脂肪酸または脂肪族アミンもしくはアミドと、酸化エチレンおよび／または酸化プロピレンとの縮合生成物；グリコール、ソルビン性アルコール、ショ糖またはペンタエリトリトールの脂肪酸エステル、ならびにこれらと酸化エチレンおよび／または酸化プロピレンとの縮合；脂肪族アルコール、またはｐ−オクチルフェノールまたはｐ−オクチルクレゾールのようなアルキルフェノールと、酸化エチレンおよび／または酸化プロピレンとの縮合生成物；これらの縮合生成物の硫酸塩またはスルホン酸塩；分子中に少なくとも１０個の炭素原子を有する硫酸またはスルホン酸エステルのアルカリ金属塩もしくはアルカリ土類金属塩、好ましくはナトリウム塩、たとえばラウリル硫酸ナトリウム、第二級アルキル硫酸ナトリウム、スルホン化ヒマシ油のナトリウム塩、およびドデシルベンゼンスルホン酸ナトリウムのようなアルキルアリールスルホン酸ナトリウムを包含する。 Surfactants may be emulsifiers, dispersants or wetting agents; they may be nonionic or ionic. Examples of suitable surfactants are sodium or calcium salts of polyacrylic acid and lignin sulfonic acid; fatty acids or aliphatic amines or amides having at least 12 carbon atoms in the molecule, ethylene oxide and / or propylene oxide Condensation products of: glycols, sorbic alcohols, fatty acid esters of sucrose or pentaerythritol, and their condensation with ethylene oxide and / or propylene oxide; aliphatic alcohols, or like p-octylphenol or p-octylcresol Condensation products of alkylphenols with ethylene oxide and / or propylene oxide; sulfates or sulfonates of these condensation products; sulfates or sulfonate esters having at least 10 carbon atoms in the molecule Lithium or alkaline earth metal salts, preferably sodium salts such as sodium lauryl sulfate, secondary sodium alkyl sulfates, sodium salts of sulfonated castor oil, and sodium alkylaryl sulfonates such as sodium dodecylbenzene sulfonate Include.
本発明による組成物および配合物の例は、湿潤性粉末、粉塵性粉末、顆粒、水溶液、乳化性濃縮物、乳濁液、懸濁液濃縮物、エアゾール組成物および燻蒸剤である。湿潤性粉末は、通常、２５、５０または７５重量％（絶対重量）の有効成分を含有し、通常、固体の不活性担体に加えて、３〜１０重量％の分散剤、ならびに必要な場合は、０〜１０重量％の安定剤、および／またはその他の添加剤、たとえば浸透剤または固着剤を含有する。粉塵性粉末は、通常、分散剤以外の湿潤性粉末と同様の組成を有する、粉塵濃縮物として配合され、更なる固体担体で希釈されて、通常０．５〜１０重量％の有効成分を含有する組成物が得られる。顆粒は、通常、１０〜１００ＢＳメッシュ（１．６７６〜０．１５２mm）の粒度を有するよう調製され、凝集または含浸技法によって製造され得る。一般に、顆粒は、０．５〜７５重量％の有効成分、および０〜１０重量％の添加剤、たとえば安定剤、界面活性剤、徐放改質剤を含有する。乳化性濃縮物は、通常、溶媒、および必要な場合は共溶媒に加えて、１〜５０％（重量／体積：ｗ／ｖ）の有効成分、２〜２０％w/vの乳化剤、および０〜２０％w/vのその他の添加剤、たとえば安定剤、浸透剤および腐食防止剤を含有する。懸濁液濃縮物は、通常、１０〜７５重量％の有効成分、０．５〜１５重量％の分散剤、０．１〜１０重量％のその他の添加剤、たとえば消泡剤、腐食防止剤、安定剤、浸透剤および固着剤を含有する。 Examples of compositions and formulations according to the invention are wettable powders, dusty powders, granules, aqueous solutions, emulsifiable concentrates, emulsions, suspension concentrates, aerosol compositions and fumigants. Wettable powders usually contain 25, 50 or 75% by weight (absolute weight) of the active ingredient, usually 3 to 10% by weight of a dispersant in addition to a solid inert carrier, and if necessary 0-10% by weight of stabilizers, and / or other additives such as penetrants or stickers. Dust powders are usually formulated as dust concentrates having the same composition as wettable powders other than dispersants, diluted with additional solid carriers and usually contain 0.5-10% by weight of active ingredient A composition is obtained. Granules are usually prepared to have a particle size of 10-100 BS mesh (1.676-0.152 mm) and can be produced by agglomeration or impregnation techniques. Generally, the granules contain 0.5-75% by weight of the active ingredient and 0-10% by weight of additives such as stabilizers, surfactants, sustained release modifiers. Emulsifiable concentrates usually contain 1-50% (weight / volume: w / v) active ingredient, 2-20% w / v emulsifier, and 0, in addition to the solvent and, if necessary, the co-solvent. Contains -20% w / v other additives such as stabilizers, penetrants and corrosion inhibitors. Suspension concentrates usually contain 10 to 75% by weight of active ingredient, 0.5 to 15% by weight of dispersant, 0.1 to 10% by weight of other additives such as antifoaming agents, corrosion inhibitors. , Containing stabilizers, penetrants and sticking agents.
本発明による湿潤性粉末または濃縮物を水で希釈することによって得られる、水性分散剤および乳濁液、たとえば組成物も、本発明の範囲内にある。該乳濁液は、油中水または水中油タイプのものでよい。 Aqueous dispersions and emulsions such as compositions obtained by diluting wettable powders or concentrates according to the invention with water are also within the scope of the invention. The emulsion may be of the water-in-oil or oil-in-water type.
１種以上のその他の殺真菌剤を加えた組成物は、一般式（Ｉ）で示される単一の化合物より広いスペクトル活性を有する、加えて、その他の殺真菌剤は、一般式（Ｉ）で示される化合物の殺真菌活性に対して相乗効果を有し得る。一般式（Ｉ）で示される化合物は、他の殺虫剤とともにか、または別の殺真菌剤およびその他の殺虫剤とともに同時に用いることもできる。 Compositions with the addition of one or more other fungicides have a broader spectrum activity than a single compound of general formula (I). In addition, other fungicides have general formula (I) It may have a synergistic effect on the fungicidal activity of the compound represented by The compounds of general formula (I) can also be used together with other insecticides or simultaneously with other fungicides and other insecticides.
本発明は、以下の利点を有する。 The present invention has the following advantages.
本発明の化合物は、広いスペクトルの殺真菌活性を有し、卵菌類、担子菌類、子嚢菌類の病原体、および不完全菌類によって引き起こされる、すべての種類の植物の疾患を防除するのに用いてよく、活性が高いために、非常に低い用量で良好な防除薬効も与え得る。これらの化合物は、浸透活性を有し、土壌および葉面殺真菌剤として用いることができる。キュウリべと病、キュウリ灰色カビ病、キュウリうどん粉病、トマト夏疫病、トマト疫病、トウガラシ疫病菌胴枯れ病、ブドウべと病、ブドウ白腐れ病、リンゴ輪腐れ病、リンゴアルテルナリア斑点病、イネ紋枯れ病、イネいもち病、コムギ赤錆病、コムギ葉枯れ病、コムギうどん粉病、ナタネスクレロチニア病、トウモロコシごま葉枯れ病の満足すべき防除を与えることができる。 The compounds of the present invention have a broad spectrum of fungicidal activity and are used to control all kinds of plant diseases caused by oomycetes, basidiomycetes, ascomycetes pathogens and incomplete fungi Well, because of its high activity, it can also give good control efficacy at very low doses. These compounds have osmotic activity and can be used as soil and foliar fungicides. Cucumber downy mildew, cucumber gray mold disease, cucumber powdery mildew, tomato summer plague, tomato plague, red pepper plague fungus blight, grape downy mildew, grape white rot, apple ring rot, apple alternaria spot disease, rice Satisfactory control of leaf blight, rice blast, wheat red rust, wheat leaf blight, wheat powdery mildew, rapeseed rot, and corn sesame leaf blight can be provided.
本発明の化合物は、非常に良好な殺虫および殺ダニ活性を有し、昆虫およびダニ類、たとえばアワヨトウムシ、コナガ、アリマキおよびイエカを防除するのに用い得る。これらの属性は、すべて、統合された昆虫管理に適切である。 The compounds of the present invention have very good insecticidal and acaricidal activity and can be used to control insects and ticks, such as scallops, diamondback moths, aphids and squids. All of these attributes are appropriate for integrated insect management.
上記により、本発明は、一般式（Ｉ）のアゾール化合物およびそれらの組成物の、植物における疾患ならびに昆虫を防除するための適用も包含する。方法の使用は、当分野の技術者に公知である。 According to the above, the present invention also encompasses the application of the azole compounds of general formula (I) and their compositions for controlling diseases in plants and insects. The use of the method is known to those skilled in the art.
以下の実施例は、本発明を例示するものである。 The following examples illustrate the invention.
製造例
実施例１
化合物２の製造
３−（４−クロロフェニル）−３−オキソプロパン酸エチル２．１２gをメタノールに溶解し、溶液を加熱還流した。僅かに過剰なメチルヒドラジンを溶液に滴加し、３時間後、反応を薄層クロマトグラフィーによって追跡し、溶液を濃縮し、冷却し、結晶を得、濾過した。残渣を、メタノールで洗浄し、乾燥し、３−（４−クロロフェニル）−１−メチル−１Ｈ−ピラゾール−５−オールの結晶１．５gを得た。
Production Example Example 1
Preparation of Compound 2 2.12 g of ethyl 3- (4-chlorophenyl) -3-oxopropanoate was dissolved in methanol, and the solution was heated to reflux. A slight excess of methyl hydrazine was added dropwise to the solution and after 3 hours the reaction was followed by thin layer chromatography, the solution was concentrated, cooled, crystals were obtained and filtered. The residue was washed with methanol and dried to obtain 1.5 g of 3- (4-chlorophenyl) -1-methyl-1H-pyrazol-5-ol crystals.
上記の３−（４−クロロフェニル）−１−メチル−１Ｈ−ピラゾール−５−オールの結晶１．０４gを、ＤＭＦ５mlに溶解し、ＮａＨ（０．３６g）を溶液に加えた。次いで、溶液を３０分間撹拌した。（Ｅ）−２−［２−（ブロモメチル）フェニル］−３−メトキシアクリル酸メチル１．４２gを加え、混合物を、４０℃に加熱した。３時間後、反応を薄層クロマトグラフィーによって追跡し、反応混合物を、ブライン５０mlに注ぎ込み、酢酸エチル１００mlで３回抽出した。一緒にした有機抽出物を、乾燥し、濃縮して、未精製生成物を得た。これを、酢酸エチルおよび石油エーテル（沸点範囲：６０〜９０℃）の１：４（容積／容積）混合物を溶離液として用いたシリカゲルカラムのクロマトグラフィーに付して、化合物２の粘稠な油１．３g（析出後に固化）を得た。 1.04 g of the above 3- (4-chlorophenyl) -1-methyl-1H-pyrazol-5-ol crystal was dissolved in 5 ml of DMF and NaH (0.36 g) was added to the solution. The solution was then stirred for 30 minutes. 1.42 g of methyl (E) -2- [2- (bromomethyl) phenyl] -3-methoxyacrylate was added and the mixture was heated to 40 ° C. After 3 hours, the reaction was followed by thin layer chromatography and the reaction mixture was poured into 50 ml brine and extracted three times with 100 ml ethyl acetate. The combined organic extracts were dried and concentrated to give the crude product. This was chromatographed on a silica gel column using a 1: 4 (volume / volume) mixture of ethyl acetate and petroleum ether (boiling range: 60-90 ° C.) as eluent to give a viscous oil of compound 2. 1.3 g (solidified after precipitation) was obtained.
実施例２
化合物６９の製造
ＮａＨ０．１５gを、フラスコに仕込み、石油エーテル、ＤＭＦ５ml、および３−（６−クロロピリジン−３−イル）−１−メチル−１Ｈ−ピラゾール−５−オール（CN1,257,490Aに従って製造）０．５gで洗浄した。室温で２分間撹拌した後に、（Ｅ）−２−［２−（ブロモメチル）フェニル］−３−メトキシアクリル酸メチル０．７gを加え、反応温度を６０℃に上げた。２時間後、反応を薄層クロマトグラフィーによって追跡し、反応混合物を、ブライン５０mlに注ぎ込み、酢酸エチル１００mlで３回抽出した。一緒にした有機抽出物を、乾燥し、濃縮して、未精製生成物を得た。未精製生成物をシリカゲルカラムを通して精製し、僅かに黄色の固体０．２gを得た。
Example 2
Preparation of Compound 69 NaH 0.15 g was charged to a flask and prepared according to petroleum ether, DMF 5 ml, and 3- (6-chloropyridin-3-yl) -1-methyl-1H-pyrazol-5-ol (CN1,257,490A). ) Washed with 0.5 g. After stirring at room temperature for 2 minutes, 0.7 g of methyl (E) -2- [2- (bromomethyl) phenyl] -3-methoxyacrylate was added and the reaction temperature was raised to 60 ° C. After 2 hours, the reaction was followed by thin layer chromatography and the reaction mixture was poured into 50 ml brine and extracted 3 times with 100 ml ethyl acetate. The combined organic extracts were dried and concentrated to give the crude product. The crude product was purified through a silica gel column to give 0.2 g of a slightly yellow solid.
実施例３
化合物８６の製造
米国特許第3,781,438号の方法に従って、３−（４−ニトロフェニル）−３−オキソプロパン酸エチル２gをメタノールに溶解し、僅かに過剰な塩酸ヒドロキシルアミン、および等価量の水酸化ナトリウムを加え、混合物を加熱還流した。３時間後、反応を、薄層クロマトグラフィーによって追跡し、水を、反応混合物に加え、酢酸エチルで抽出し、乾燥し、濃縮して、３−（４−ニトロフェニル）イソオキサゾール−５−オールを固体として得た。
Example 3
Preparation of Compound 86 According to the method of US Pat. No. 3,781,438, 2 g of ethyl 3- (4-nitrophenyl) -3-oxopropanoate is dissolved in methanol, slightly excess hydroxylamine hydrochloride and an equivalent amount of sodium hydroxide Was added and the mixture was heated to reflux. After 3 hours, the reaction was followed by thin layer chromatography, water was added to the reaction mixture, extracted with ethyl acetate, dried and concentrated to 3- (4-nitrophenyl) isoxazol-5-ol. Was obtained as a solid.
上記の３−（４−ニトロフェニル）イソオキサゾール−５−オールの結晶１gをＤＭＦに溶解し、ＮａＨ０．４gを溶液に加え、次いで、溶液を３０分間撹拌した。（Ｅ）−２−［２−（ブロモメチル）フェニル］−３−メトキシアクリル酸メチル１．４gを加え、混合物を５０℃に加熱した。６時間後、反応を薄層クロマトグラフィーによって追跡し、反応混合物を、ブライン５０mlに注ぎ込み、酢酸エチル１００mlで３回抽出した。一緒にした有機抽出物を、乾燥し、濃縮し、未精製生成物をシリカゲルカラムを通して精製して、化合物１．５gを固体として得た。 1 g of the above 3- (4-nitrophenyl) isoxazol-5-ol crystals was dissolved in DMF, 0.4 g of NaH was added to the solution, and then the solution was stirred for 30 minutes. 1.4 g of methyl (E) -2- [2- (bromomethyl) phenyl] -3-methoxyacrylate was added and the mixture was heated to 50 ° C. After 6 hours, the reaction was followed by thin layer chromatography and the reaction mixture was poured into 50 ml brine and extracted three times with 100 ml ethyl acetate. The combined organic extracts were dried and concentrated, and the crude product was purified through a silica gel column to give 1.5 g of compound as a solid.
実施例４
化合物１７９の製造
化合物１７２（実施例１に従って製造）０．２g、４−クロロフェニルボロン酸０．０８g、無水炭酸カリウム０．２g、および酢酸テトラキス（フェニル）ホスフィンパラジウム０．０１gをトルエン１０ml中で加えた混合物を、１８時間加熱還流し、室温に冷却し、濾過した。母液を濃縮し、シリカゲルカラムを通して精製して、化合物０．２gを固体として得た。
Example 4
Preparation of Compound 179 Compound 172 (prepared according to Example 1) 0.2 g, 4-chlorophenylboronic acid 0.08 g, anhydrous potassium carbonate 0.2 g, and tetrakis (phenyl) phosphine palladium acetate 0.01 g are added in 10 ml of toluene. The resulting mixture was heated to reflux for 18 hours, cooled to room temperature and filtered. The mother liquor was concentrated and purified through a silica gel column to give 0.2 g of compound as a solid.
実施例５
化合物２４８の製造
ＤＭＦ（１５ml）中の３−（４−クロロフェニル）−１−メチル−１−１Ｈ−ピラゾール−５−オール（１．０g）、（Ｅ）−２−［２−（ブロモメチル）フェニル］−２−（メトキシイミノ）酢酸メチル（１．５g）、および無水炭酸カリウム（２．１g）の混合物を撹拌し、７０〜８０℃で７時間反応させ（反応は、薄層クロマトグラフィーによって追跡した）、次いで、ブライン１００mlに注ぎ込み、酢酸エチル１００mlで３回抽出した。一緒にした有機抽出物を、乾燥し、濃縮した。未精製生成物をシリカゲルカラムを通して精製して、１．１gの化合物２４８を固体として得た。
Example 5
Preparation of compound 248 3- (4-Chlorophenyl) -1-methyl-l lH-pyrazol-5-ol (1.0 g), (E) -2- [2- (bromomethyl) phenyl in DMF (15 ml) ] A mixture of methyl 2- (methoxyimino) acetate (1.5 g) and anhydrous potassium carbonate (2.1 g) was stirred and reacted at 70-80 ° C. for 7 hours (reaction followed by thin layer chromatography). Then poured into 100 ml of brine and extracted three times with 100 ml of ethyl acetate. The combined organic extracts were dried and concentrated. The crude product was purified through a silica gel column to give 1.1 g of compound 248 as a solid.
実施例６
化合物３５６の製造
０．２gの化合物２４８を、ＴＨＦ５mlに溶解し、僅かに過剰なメチルアミン溶液（２５〜３０％）を溶液に滴加した。混合物を、１時間還流し（反応は、薄層クロマトグラフィーによって追跡した）、次いで濃縮した。残渣に水を加え、酢酸エチル１０mlで３回抽出し、一緒にした有機抽出物を、乾燥し、濃縮した。未精製生成物をシリカゲルカラムを通して精製して、０．１６gの化合物３５６を固体として得た。
Example 6
Preparation of Compound 356 0.2 g of Compound 248 was dissolved in 5 ml of THF and a slight excess of methylamine solution (25-30%) was added dropwise to the solution. The mixture was refluxed for 1 hour (the reaction was followed by thin layer chromatography) and then concentrated. Water was added to the residue, extracted three times with 10 ml of ethyl acetate, and the combined organic extracts were dried and concentrated. The crude product was purified through a silica gel column to give 0.16 g of compound 356 as a solid.
その他の化合物を、上記の実施例に従って製造した。 Other compounds were prepared according to the above examples.
配合例 １００％の有効成分を基準として（重量／重量％） Formulation example Based on 100% active ingredient (weight / weight%)
実施例７
６０％の湿潤性粉末
化合物６９ ６０％
ドデシルナフタレン硫酸ナトリウム ２％
リグノ硫酸ナトリウム ９％
陶土 １００％まで補充
すべての固体成分を充分に混合し、粒度が６０％湿潤性粉末を得るための基準（≦４４μm）に達するまで、粉砕した。
Example 7
60% wettable powder compound 69 60%
Sodium dodecyl naphthalene sulfate 2%
Sodium lignosulfate 9%
Replenish to 100% porcelain All solid ingredients were mixed well and ground until the particle size reached the standard (≦ 44 μm) to obtain a 60% wettable powder.
実施例８
３５％の乳濁濃縮液
化合物２ ３５％
リン酸 １０％
エチレンオキシ脂肪酸グリセリンエステル １５％
シクロヘキサノン １００％まで補充
リン酸をシクロヘキサノンに溶解し、次いで、化合物２およびエチレンオキシ脂肪酸グリセリンエステルを加え、透明溶液中の乳濁液、すなわち３５％の乳濁濃縮液を、最終的に得た。
Example 8
35% emulsion concentrate compound 2 35%
Phosphoric acid 10%
Ethyleneoxy fatty acid glycerin ester 15%
Cyclohexanone replenished to 100% Phosphoric acid was dissolved in cyclohexanone, then compound 2 and ethyleneoxy fatty acid glycerin ester were added to finally obtain an emulsion in clear solution, ie 35% emulsion concentrate.
実施例９
３０％の水性懸濁液
化合物２８７ ３０％
ドデシルナフタレン硫酸ナトリウム ４％
ヘミセルロース ２％
エポキシプロパン ８％
水 １００％まで補充
化合物２８７、加えるべき量の８０％の水、およびドデシルナフタレン硫酸ナトリウムの混合物を、粉砕機（１mmのボール）内で粉砕した。その他の成分を水の残量に溶解し、撹拌下で加えて、３０％の水性懸濁液を得た。
Example 9
30% aqueous suspension compound 287 30%
Sodium dodecyl naphthalene sulfate 4%
Hemicellulose 2%
Epoxypropane 8%
Water replenished to 100% A mixture of compound 287, 80% of the water to be added, and sodium dodecylnaphthalene sulfate was ground in a grinder (1 mm ball). The other ingredients were dissolved in the remaining amount of water and added under stirring to give a 30% aqueous suspension.
実施例１０
２５％の懸濁乳濁液
化合物１２ ２５％
アルキルスルホン酸塩（乳化剤１） ４％
エチレンオキシ脂肪酸グリセリンエステル（乳化剤２） ２％
ドデシルベンゼン硫酸カルシウム（乳化剤３） １．５％
ポリエチレンオキシアルキルプロピルエーテル（分散剤） ２．５％
シクロヘキサノン（溶媒１） ３０％
石油留分（沸点＞２００℃）（溶媒２） １００％まで補充
化合物１２を、加えるべき量の８０％の溶媒に溶解し、次いで、乳化剤および分散剤を加え、混合物を、完全に撹拌し、粉砕機（１mmのボール）内で粉砕した。その他の溶媒を加えた。
Example 10
25% suspension emulsion compound 12 25%
Alkyl sulfonate (Emulsifier 1) 4%
Ethyleneoxy fatty acid glycerin ester (Emulsifier 2) 2%
Calcium dodecylbenzene sulfate (Emulsifier 3) 1.5%
Polyethyleneoxyalkyl propyl ether (dispersant) 2.5%
Cyclohexanone (solvent 1) 30%
Petroleum fraction (boiling point> 200 ° C.) (solvent 2) replenished to 100% Compound 12 is dissolved in the amount of 80% solvent to be added, then emulsifier and dispersant are added, the mixture is stirred thoroughly, Grind in a grinder (1 mm ball). Other solvents were added.
生物学的試験
実施例１１
殺真菌活性の決定
選ばれた化合物の植物疾患に対する殺真菌活性の決定を、以下の手順によって実施した：
技術的サンプルを、ＤＭＦに溶解し、０．１％のトゥイーン８０を含有する水で必要とされる濃度まで希釈した。試験溶液を、鉢植えの植物に吹き付けた。２４時間後に、病原体接種を実施し、次いで、植物を、効果のための一定の温度および水分を有する栽培室内に保持した。未処理植物が望ましい疾患の重篤度になったとき（ほぼ１週間後）、肉眼による観察によって、査定を実施した。
Biological Test Example 11
Determination of fungicidal activity The determination of fungicidal activity of selected compounds against plant diseases was carried out by the following procedure:
Technical samples were dissolved in DMF and diluted to the required concentration with water containing 0.1% Tween 80. The test solution was sprayed onto potted plants. After 24 hours, pathogen inoculation was performed and the plants were then kept in a cultivation room with constant temperature and moisture for effect. When the untreated plants had the desired disease severity (after approximately one week), the assessment was performed by visual observation.
試験結果の一部：
５００ppmでは、化合物１、２、４、５、１１、１２、３０、６９、７４、８３、８４、８６、１６５、１７４、１７９、１９０、２４８、２８７、３５６、４３５は、コムギうどん粉病に対して１００％の防除を示した。
Some of the test results:
At 500 ppm, compounds 1, 2, 4, 5, 11, 12, 30, 69, 74, 83, 84, 86, 165, 174, 179, 190, 248, 287, 356, 435 are against wheat powdery mildew. Showed 100% control.
５００ppmでは、化合物１、２、４、５、１１、１２、３０、６９、７４、８３、８４、８６、１９０、２４８、２８７は、キュウリべと病に対して１００％の防除を示した。 At 500 ppm, compounds 1, 2, 4, 5, 11, 12, 30, 69, 74, 83, 84, 86, 190, 248, 287 showed 100% control against cucumber downy mildew.
５００ppmでは、化合物１５１、２４７は、キュウリ灰色カビ病およびコムギうどん粉病に対して１００％の防除を示した。 At 500 ppm, compounds 151 and 247 showed 100% control against cucumber gray mold and wheat powdery mildew.
５０ppmでは、化合物１、２、４、５、３０、６９、８４、８６、２８７は、キュウリべと病およびコムギうどん粉病に対する１００％の防除を示した。 At 50 ppm, compounds 1, 2, 4, 5, 30, 69, 84, 86, 287 showed 100% control against cucumber downy mildew and wheat powdery mildew.
１００ppmでは、化合物２は、リンゴ輪腐れ病、コムギ赤カビ病、ナタネスクレロチニア病、ブドウ白腐れ病、リンゴアルテルナリア斑点病、トマト夏疫病、トウモロコシごま葉枯れ病、およびナタネべと病に対して８０％を上回る防除を示した。 At 100 ppm, compound 2 is effective in apple ring rot, wheat red mold disease, rapeseed rot rot, grape white rot, apple alternaria spot disease, tomato summer plague, corn sesame leaf blight, and rape The control over 80% was shown.
実施例１２
殺虫および殺ダニ活性の決定
選ばれた化合物の植物疾患に対する殺虫および殺ダニ活性の決定を、以下の手順によって実施した：
技術的サンプルを、アセトンに溶解し、０．１％のトゥイーン８０を含有する水で必要とされる濃度まで希釈した。アワヨトウムシ、コナガおよびモモアカアリマキを、ポッター噴霧塔を用いて処理し、イエカを、浸漬培養法を用いて処理した。処理の２〜３日後に、試験昆虫の死亡率調査を実施した。
Example 12
Determination of insecticidal and acaricidal activity Determination of the insecticidal and acaricidal activity of selected compounds against plant diseases was carried out by the following procedure:
The technical sample was dissolved in acetone and diluted to the required concentration with water containing 0.1% Tween 80. Acacia weevil, diamondback moth and peach mosquito were treated using a potter spray tower, and cuttlefish were treated using an immersion culture method. Two to three days after treatment, a test insect mortality survey was performed.
試験結果の一部
１５０ppmでは、化合物３０は、アワヨトウムシ、コナガ、アリマキおよびイエカの１００％の防除を示した。
At 150 ppm, part of the test results, Compound 30 showed 100% control of scallops, diamondback moths, aphids and squids.
Claims (9)
［式中、Ｘ1は、ＣＨまたはＮから選ばれ；Ｘ2は、Ｏ、ＳまたはＮＲ7から選ばれ；Ｘ3は、Ｏ、ＳまたはＮＲ8から選ばれ；
Ａ1は、ＮまたはＣＲ9から選ばれ；Ａ2は、ＮまたはＣＲ10から選ばれ；Ａ3は、ＮまたはＣＲ11から選ばれ；Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2は、同じであっても、異なってもよくて、Ｈ、Ｃ1〜Ｃ12アルキルまたはＣ1〜Ｃ12ハロアルキルから選ばれ；
Ｒ3は、Ｈ、ハロ、Ｃ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルキルまたはＣ1〜Ｃ12アルコキシから選ばれ；
Ｒ7は、ＨまたはＣ1〜Ｃ12アルキルから選ばれ；
Ｒ8は、Ｈ、Ｃ1〜Ｃ12アルキル；Ｃ1〜Ｃ12ハロアルキル；Ｃ1〜Ｃ12アルコキシカルボニルまたはＣ1〜Ｃ12アルコキシカルボニルＣ1〜Ｃ12アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11は、同じであっても、異なってもよくて、Ｈ、ハロ、ＮＯ2、ＣＮ、ＣＯＮＨ2、ＣＨ2ＣＯＮＨ2、ＣＨ2ＣＮ、Ｃ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルキル、Ｃ1〜Ｃ12アルコキシ、Ｃ1〜Ｃ12ハロアルコキシ、Ｃ1〜Ｃ12アルキルチオ、Ｃ1〜Ｃ12アルキルスルホニル、Ｃ1〜Ｃ12アルキルカルボニル、Ｃ1〜Ｃ12アルコキシＣ1〜Ｃ12アルキル、Ｃ1〜Ｃ12アルコキシカルボニル、Ｃ1〜Ｃ12アルコキシカルボニルＣ1〜Ｃ12アルキル、Ｃ1〜Ｃ12ハロアルコキシＣ1〜Ｃ12アルキルから選ばれることができ、基は、他の任意の基：アミノＣ1〜Ｃ12アルキル、アリール、ヘテロアリールで置換されていてもよく；アロキシル、アリールＣ1〜Ｃ12アルキル、アリールＣ1〜Ｃ12アルコキシ、ヘテロアリールＣ1〜Ｃ12アルキルもしくはヘテロアリールＣ1〜Ｃ12アルコキシから選ばれる］
で示される置換アゾール化合物および立体異性体。 Formula (I):
[Wherein X 1 is selected from CH or N; X 2 is selected from O, S or NR 7 ; X 3 is selected from O, S or NR 8 ;
A 1 is selected from N or CR 9 ; A 2 is selected from N or CR 10 ; A 3 is selected from N or CR 11 ; if N is selected, then A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 may be the same or different and are selected from H, C 1 -C 12 alkyl or C 1 -C 12 haloalkyl;
R 3 is selected from H, halo, C 1 -C 12 alkyl, C 1 -C 12 haloalkyl or C 1 -C 12 alkoxy;
R 7 is selected from H or C 1 -C 12 alkyl;
R 8 is selected from H, C 1 -C 12 alkyl; C 1 -C 12 haloalkyl; C 1 -C 12 alkoxycarbonyl or C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and may be H, halo, NO 2 , CN, CONH 2 , CH 2 CONH 2 , CH 2. CN, C 1 ~C 12 alkyl, C 1 -C 12 haloalkyl, C 1 -C 12 alkoxy, C 1 -C 12 haloalkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl, C 1 -C 12 alkoxy C 1 -C 12 alkyl, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkoxycarbonyl C 1 -C 12 alkyl, C 1 -C 12 haloalkoxy C 1 -C 12 alkyl may be selected, the group may be substituted with any other group: amino C 1 -C 12 alkyl, aryl, heteroaryl; aroxyl, aryl C 1 -C 12 alkyl, aryl C 1 ~C 12 alkoxy It is selected from heteroaryl C 1 -C 12 alkyl or heteroaryl C 1 -C 12 alkoxy]
Substituted azole compounds and stereoisomers of
Ｘ1が、ＣＨまたはＮから選ばれ；Ｘ2が、Ｏ、ＳまたはＮＲ7から選ばれ；Ｘ3が、Ｏ、ＳまたはＮＲ8から選ばれ；
Ａ1が、ＮまたはＣＲ9から選ばれ、Ａ2が、ＮまたはＣＲ10から選ばれ、Ａ3が、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2が、同じであっても、異なってもよくて、Ｈ、Ｃ1〜Ｃ6アルキルまたはＣ1〜Ｃ6ハロアルキルから選ばれ；
Ｒ3が、Ｈ、ハロ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキルまたはＣ1〜Ｃ6アルコキシから選ばれ；
Ｒ7が、ＨまたはＣ1〜Ｃ6アルキルから選ばれ；
Ｒ8が、Ｈ、Ｃ1〜Ｃ6アルキル；Ｃ1〜Ｃ6ハロアルキル；Ｃ1〜Ｃ6アルコキシカルボニルまたはＣ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11が、同じであっても、異なってもよくて、Ｈ、ハロ、ＮＯ2、ＣＮ、ＣＯＮＨ2、ＣＨ2ＣＯＮＨ2、ＣＨ2ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルコキシＣ1〜Ｃ6アルキルから選ばれ、基は、任意の他の基：アミノＣ1〜Ｃ6アルキル、アリール、ヘテロアリールで置換されていてもよく；アロキシル、アリールＣ1〜Ｃ6アルキル、アリールＣ1〜Ｃ6アルコキシ、ヘテロアリールＣ1〜Ｃ6アルキルもしくはヘテロアリールＣ1〜Ｃ6アルコキシから選ばれることを特徴とする、請求項１記載の置換アゾール化合物。 In general formula (I):
X 1 is selected from CH or N; X 2 is selected from O, S or NR 7 ; X 3 is selected from O, S or NR 8 ;
If A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 and A 3 is selected from N or CR 11 and selected from N, then A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 may be the same or different and are selected from H, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
R 3 is selected from H, halo, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl or C 1 -C 6 alkoxy;
R 7 is selected from H or C 1 -C 6 alkyl;
R 8 is selected from H, C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 6 alkoxycarbonyl or C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and H, halo, NO 2 , CN, CONH 2 , CH 2 CONH 2 , CH 2 CN, C 1 ~C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy C 1 -C Selected from 6 alkyl, the group may be substituted with any other group: amino C 1 -C 6 alkyl, aryl, heteroaryl; aroxyl, aryl C 1 -C 6 alkyl, aryl C 1 -C 6 alkoxy, heteroaryl C 1 ~ It characterized in that it is selected from C 6 alkyl or heteroaryl C 1 -C 6 alkoxy, claim 1 substituted azole compounds according.
Ｘ1が、ＣＨまたはＮから選ばれ；Ｘ2が、ＯまたはＮＨから選ばれ；Ｘ3が、Ｏ、ＳまたはＮＲ8から選ばれ；
Ａ1が、ＮまたはＣＲ9から選ばれ、Ａ2が、ＮまたはＣＲ10から選ばれ、Ａ3が、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2が、ＣＨ3であり；
Ｒ3が、ＨまたはＣＨ3から選ばれ；
Ｒ8が、Ｈ、Ｃ1〜Ｃ6アルキル；Ｃ1〜Ｃ6ハロアルキル；Ｃ1〜Ｃ3アルコキシカルボニルまたはＣ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ3アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11が、同じであっても、異なってもよくて、Ｈ、ハロ、ＮＯ2、ＣＮ、ＣＯＮＨ2、ＣＨ2ＣＯＮＨ2、ＣＨ2ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルコキシＣ1〜Ｃ6アルキルから選ばれ、基は、任意の他の基：アミノＣ1〜Ｃ3アルキル、フェニル、フェノキシ、ベンジルもしくはベンジルオキシで置換されていてもよいことを特徴とする、請求項２記載の置換アゾール化合物。 In general formula (I):
X 1 is selected from CH or N; X 2 is selected from O or NH; X 3 is selected from O, S or NR 8 ;
If A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 and A 3 is selected from N or CR 11 and selected from N, then A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 are CH 3 ;
R 3 is selected from H or CH 3 ;
R 8 is selected from H, C 1 -C 6 alkyl; C 1 -C 6 haloalkyl; C 1 -C 3 alkoxycarbonyl or C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and H, halo, NO 2 , CN, CONH 2 , CH 2 CONH 2 , CH 2 CN, C 1 ~C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy C 1 -C Substitution according to claim 2, characterized in that it is selected from 6 alkyl and the group is optionally substituted by any other group: amino C 1 -C 3 alkyl, phenyl, phenoxy, benzyl or benzyloxy An azole compound.
Ｘ1が、ＣＨまたはＮから選ばれ；Ｘ2が、ＯまたはＮＨから選ばれ；Ｘ3が、ＯまたはＮＲ8から選ばれ；
Ａ1が、ＮまたはＣＲ9から選ばれ、Ａ2が、ＮまたはＣＲ10から選ばれ、Ａ3が、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2が、ＣＨ3であり；
Ｒ3が、Ｈであり；
Ｒ8が、Ｈ、Ｃ1〜Ｃ3アルキル；Ｃ1〜Ｃ3ハロアルキル；Ｃ1〜Ｃ3アルコキシカルボニルまたはＣ1〜Ｃ3アルコキシカルボニルＣ1〜Ｃ3アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11が、同じであっても、異なってもよくて、Ｈ、Ｃｌ、Ｂｒ、Ｆ、ＮＯ2、ＣＮ、ＣＨ2ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ3アルキル、Ｃ1〜Ｃ3ハロアルコキシＣ1〜Ｃ3アルキル、置換アミノＣ1〜Ｃ3アルキル、フェニルもしくは置換フェニル、フェノキシもしくは置換フェノキシから選ばれることを特徴とする、請求項３記載の置換アゾール化合物。 In general formula (I):
X 1 is selected from CH or N; X 2 is selected from O or NH; X 3 is selected from O or NR 8 ;
If A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 and A 3 is selected from N or CR 11 and selected from N, then A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 are CH 3 ;
R 3 is H;
R 8 is selected from H, C 1 -C 3 alkyl; C 1 -C 3 haloalkyl; C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxycarbonyl C 1 -C 3 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different, and H, Cl, Br, F, NO 2 , CN, CH 2 CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 3 alkyl, C 1 -C 3 haloalkoxy C 1 -C 3 alkyl, substituted amino C 1 -C 3 alkyl, phenyl or substituted phenyl, characterized in that it is selected from phenoxy or substituted phenoxy, claim 3 substituted azole compounds according.
Ｘ1が、ＣＨまたはＮから選ばれ；Ｘ2が、ＯまたはＮＨから選ばれ；Ｘ3が、ＯまたはＮＲ8から選ばれ；
Ａ1が、ＮまたはＣＲ9から選ばれ、Ａ2が、ＮまたはＣＲ10から選ばれ、Ａ3が、ＮまたはＣＲ11から選ばれ、Ｎから選ばれるならば、Ａ1、Ａ2またはＡ3の一つのみがＮから選ばれ；
Ｒ1、Ｒ2が、ＣＨ3であり；
Ｒ3が、Ｈであり；
Ｒ8が、Ｈ、Ｃ1〜Ｃ3アルキル；Ｃ1〜Ｃ3ハロアルキル；Ｃ1〜Ｃ3アルコキシカルボニルまたはＣ1〜Ｃ3アルコキシカルボニルＣ1〜Ｃ3アルキルから選ばれ；
Ｒ4、Ｒ5、Ｒ6、Ｒ9、Ｒ10およびＲ11が、同じであっても、異なってもよくて、Ｈ、Ｃｌ、Ｂｒ、Ｆ、ＮＯ2、ＣＮ、Ｃ1〜Ｃ6アルキル、Ｃ1〜Ｃ6ハロアルキル、Ｃ1〜Ｃ6アルコキシ、Ｃ1〜Ｃ6ハロアルコキシ、Ｃ1〜Ｃ6アルキルチオ、Ｃ1〜Ｃ6アルキルスルホニル、Ｃ1〜Ｃ6アルキルカルボニル、Ｃ1〜Ｃ6アルコキシカルボニル、Ｃ1〜Ｃ6アルコキシカルボニルＣ1〜Ｃ6アルキル、Ｃ1〜Ｃ6アルコキシＣ1〜Ｃ3アルキル、フェニルもしくはハロフェニル、フェノキシもしくはハロフェノキシから選ばれることを特徴とする、請求項４記載の置換アゾール化合物。 In general formula (I):
X 1 is selected from CH or N; X 2 is selected from O or NH; X 3 is selected from O or NR 8 ;
If A 1 is selected from N or CR 9 , A 2 is selected from N or CR 10 and A 3 is selected from N or CR 11 and selected from N, then A 1 , A 2 or A Only one of 3 is chosen from N;
R 1 and R 2 are CH 3 ;
R 3 is H;
R 8 is selected from H, C 1 -C 3 alkyl; C 1 -C 3 haloalkyl; C 1 -C 3 alkoxycarbonyl or C 1 -C 3 alkoxycarbonyl C 1 -C 3 alkyl;
R 4 , R 5 , R 6 , R 9 , R 10 and R 11 may be the same or different and may be H, Cl, Br, F, NO 2 , CN, C 1 -C 6 alkyl. , C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 3 alkyl, phenyl or halophenyl, characterized in that it is selected from phenoxy or halophenoxy, claim 4. The substituted azole compound according to 4.
［式中、Ｒは、離脱基、たとえばＣｌまたはＢｒである］
によって製造することができることを特徴とする方法、置換アゾール化合物およびその製造法、ならびにその使用。 It is a manufacturing method of the substituted azole compound of Claim 1, Comprising: General formula (I) is an azole compound which has a hydroxyl group shown by general formula (III), and halomethylbenzene shown by general formula (IV). Reaction in the presence of a base:
[Wherein R is a leaving group such as Cl or Br]
, Substituted azole compounds and processes for their preparation, and their use.
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| CNB2004100211723A CN1305858C (en) | 2004-02-20 | 2004-02-20 | Substituted azole compounds and their preparation and application |
| PCT/CN2005/000195 WO2005080344A1 (en) | 2004-02-20 | 2005-02-17 | Substituted azole compounds and thereof preparation and application |
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| US (1) | US7795179B2 (en) |
| EP (1) | EP1717231B1 (en) |
| JP (1) | JP4682315B2 (en) |
| CN (2) | CN1305858C (en) |
| BR (1) | BRPI0507743B1 (en) |
| DK (1) | DK1717231T3 (en) |
| WO (1) | WO2005080344A1 (en) |
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| CN1305858C (en) * | 2004-02-20 | 2007-03-21 | 沈阳化工研究院 | Substituted azole compounds and their preparation and application |
| CN100427481C (en) | 2005-05-26 | 2008-10-22 | 沈阳化工研究院 | An arylether kind compound and its preparation and application |
| CN102578130B (en) * | 2007-10-09 | 2013-04-17 | 中国中化股份有限公司 | Fungicidal composition |
| CN102511490B (en) * | 2007-10-09 | 2013-06-19 | 中国中化股份有限公司 | Fungus killing composition |
| CN102578125B (en) * | 2007-10-09 | 2013-09-11 | 中国中化股份有限公司 | Fungicidal composition |
| CN102578100B (en) * | 2007-10-09 | 2013-07-10 | 中国中化股份有限公司 | Antifungal composition |
| CN102422837B (en) * | 2007-10-09 | 2013-04-03 | 中国中化股份有限公司 | Antifungal composition |
| CN101406191B (en) * | 2007-10-09 | 2012-05-09 | 中国中化股份有限公司 | Fungicidal compositions |
| JP2011201850A (en) | 2010-03-03 | 2011-10-13 | Sumitomo Chemical Co Ltd | Plant disease controlling composition and method for controlling plant disease |
| CN102746282B (en) * | 2011-04-21 | 2014-08-20 | 中国农业大学 | N-5-substituted phenyl-2-furoyl compounds, preparation method and application thereof |
| CN102993100B (en) * | 2011-09-19 | 2014-10-22 | 中国中化股份有限公司 | Substituted pyrazole (sulphur) ketone compound and application thereof |
| CN103102308B (en) * | 2011-11-11 | 2015-04-22 | 中国中化股份有限公司 | Method of preparing pyraoxystrobin |
| CN103387540B (en) * | 2012-05-10 | 2015-10-14 | 中国中化股份有限公司 | A kind of salt forming method prepares the method for azoles bacterium ester |
| CN103387542B (en) * | 2012-05-10 | 2016-01-20 | 中国中化股份有限公司 | The preparation method of substituted pyrazolecarboxylic ether compound |
| CN103387541B (en) * | 2012-05-10 | 2016-02-10 | 中国中化股份有限公司 | A kind of preparation method of substituted pyrazolecarboxylic ether compound |
| CN103503895B (en) * | 2012-06-19 | 2015-10-21 | 中国中化股份有限公司 | A kind of Fungicidal composition containing pyrazole compound and triazole class compounds |
| CN103719094B (en) * | 2012-10-13 | 2016-08-31 | 海利尔药业集团股份有限公司 | A kind of bactericidal composition containing pyraoxystrobin Yu ferimzone |
| CN103719097A (en) * | 2012-10-16 | 2014-04-16 | 海利尔药业集团股份有限公司 | Sterilization composition containing pyraoxystrobin and azoxystrobin |
| CN103202301A (en) * | 2012-11-02 | 2013-07-17 | 海利尔药业集团股份有限公司 | Bactericidal composition containing pyraoxystrobin and mepanipyrim |
| BR112016001979B1 (en) * | 2013-07-31 | 2020-03-17 | Sumitomo Chemical Company, Limited | TETRAZOLINONE AND PIRAZOL COMPOUNDS, USES OF THE SAME, AGENT AND METHOD FOR PEST CONTROL |
| CN103563947B (en) * | 2013-11-19 | 2015-08-19 | 中国中化股份有限公司 | A kind of Fungicidal composition and application thereof |
| CN105557703B (en) * | 2014-11-07 | 2019-03-01 | 沈阳中化农药化工研发有限公司 | It is a kind of prevent and treat rice blast oil-suspending agent and its application |
| CN107474004B (en) * | 2016-06-07 | 2022-07-19 | 中国科学院上海有机化学研究所 | Trifluoromethyl quaternary carbon center compound and preparation method and application thereof |
| CN108069984B (en) * | 2016-11-18 | 2021-02-05 | 沈阳中化农药化工研发有限公司 | Substituted five-membered heterocyclic compound containing pyrimido ring and preparation method and application thereof |
| CN107347933A (en) * | 2017-08-01 | 2017-11-17 | 河南柏裕植物免疫科技有限公司 | Fruit white rot of grape vaccine |
| CN107674027B (en) * | 2017-10-25 | 2020-03-27 | 河南衡谱分析检测技术有限公司 | 13C-marked pyraoxystrobin and synthetic method thereof |
| CN110194742B (en) * | 2018-02-27 | 2020-12-25 | 浙江工业大学 | Substituted (hetero) aryl methylene pyrazole ether compound and preparation method and application thereof |
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| Publication number | Publication date |
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| BRPI0507743B1 (en) | 2018-11-21 |
| DK1717231T3 (en) | 2015-12-07 |
| US20080108668A1 (en) | 2008-05-08 |
| CN1305858C (en) | 2007-03-21 |
| BRPI0507743A (en) | 2007-07-10 |
| WO2005080344A1 (en) | 2005-09-01 |
| EP1717231A1 (en) | 2006-11-02 |
| CN1657524A (en) | 2005-08-24 |
| CN100503576C (en) | 2009-06-24 |
| EP1717231A4 (en) | 2010-11-17 |
| CN1906171A (en) | 2007-01-31 |
| EP1717231B1 (en) | 2015-09-02 |
| US7795179B2 (en) | 2010-09-14 |
| JP4682315B2 (en) | 2011-05-11 |
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